ethyl (Z)-3-<(4S-trans)-2,2-dimethyl-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>propenoate

Base Information

• Chemical Name: ethyl (Z)-3-<(4S-trans)-2,2-dimethyl-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>propenoate
• CAS No.: 90661-38-4
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386

Synonyms:ethyl (Z)-3-<(4S-trans)-2,2-dimethyl-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>propenoate

Chemical Property of ethyl (Z)-3-<(4S-trans)-2,2-dimethyl-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>propenoate

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Technology Process of ethyl (Z)-3-<(4S-trans)-2,2-dimethyl-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>propenoate

There total 15 articles about ethyl (Z)-3-<(4S-trans)-2,2-dimethyl-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>propenoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl 3-((4S,5S)-5-(benzyloxy methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate (90661-38-4,90661-39-5,91548-58-2,91548-59-3)

Guidance literature:

In methanol; Ambient temperature;

DOI:10.1016/S0040-4020(01)97597-0

Reference yield: 75.0%

2-benzyloxy-1-methylpyridinium triflate (882980-43-0) + (E)-ethyl 3-[(4S,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate (1300690-07-6) → ethyl 3-((4S,5S)-5-(benzyloxy methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate (90661-38-4,90661-39-5,91548-58-2,91548-59-3)

Guidance literature:

With magnesium oxide; In α,α,α-trifluorotoluene; at 83 ℃; for 66h; Inert atmosphere;

DOI:10.1021/jo200019j

Reference yield: 36.0%

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (Z)-3-<(4S-trans)-2,2-dimethyl-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>propenoate (90661-38-4) + (E)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate (90661-39-5)

Guidance literature:

With benzoic acid; In benzene; for 4h; Heating;

upstream raw materials:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

ethyl (triphenylphosphoranylidene)acetate

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

2,3-O-isopropylidene-L-threitol

Downstream raw materials:

(S)-5-((S)-2'-(benzyloxy)-1-hydroxyethyl)furan-2(5H)-one

(5S,6S)-6-Benzyloxymethyl-5-hydroxy-5,6-dihydro-pyran-2-one

(E)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-prop-2-en-1-ol

(-)-Se-phenyl (4S,5S)-4,5-(isopropylidenedioxy)selenohept-6-enoate

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